Table 1 Optimization of the reaction


Entry	Deviation from standard conditions	Yield %^a
1	None	84 (77)^b
2	C(+)/Cu(−) instead of C(+)/C(−)	41
3	C(+)/Fe(−) instead of C(+)/C(−)	37
4	MeCN instead of DMA	trace
5	DMSO instead of DMA	21
6	DMF instead of DMA	72
7	LiClO₄ instead of ⁿBu₄NClO₄	44
8	ⁿBu₄NI instead of ⁿBu₄NClO₄	53
9	no 20 mol% Cp₂Fe	72
10	no electricity	NR
11	under air	24
12	25 °C instead of 60 °C	53
13	2 equiv. 2 instead of 3 equiv.	67

NR no reaction.
^aReaction conditions: 4-nitrobenzonitrile 1 (0.2 mmol), carbazate 2 (0.6 mmol), ⁿBu₄NClO₄ (0.2 mmol), Cp₂Fe (0.2 equiv.), DMA (3 mL), graphite anode, graphite cathode, under argon, 60 °C, R = 1000 rpm, 10 mA, 6 h (11.2 F/mol). GC yield using dodecane as internal standard.
^bisolated yields.

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